The biggest roadblock keeping you from your goals is that nagging feeling in the back of your head saying, "I might fail."
Completing the Stranger Challenge subjects you to failure and rejection. You learn to stop letting that fear hold you back.
I cheated, she was my cocktail waitress, so I was bound to talk to her sooner or later... but I was very surprised, I found this to be a LOT harder then I originally thought it would be... maybe because I'm being put on blast... not too sure. She asked me what it was for, and I told her, and it was actually pretty cool. :)